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When it comes to Hollywood’s top names, Matt Damon definitely fits the bill. He’s been in the game for a long time, having kicked off his career at a young age. By the 1990s, he was already considered one of the rising stars, right up there with Tom Cruise, Brad Pitt, and Leonardo DiCaprio. As the years went by, he gained even more recognition, starring in films that are still iconic today.

Matt Damon in Jason Bourne (Credits: Universal Pictures)

Damon dives into a range of genres, though he’s best known for his action films. Over his career, he’s been nominated for numerous awards and even won an Oscar and a Golden Globe. Despite this, there are still a few of his films that haven’t gotten the attention they deserve and could definitely use more spotlight and reviews.

1The Talented Mr. Ripley(1999)

AlthoughThe Talented Mr. Ripleywas one of the films that really launchedMatt Damonto new heights, it’s one of those works that has faded from the spotlight over time, particularly among newer generations.

Based on the classic book of the same name, Damon plays Tom Ripley, a highly skilled and deceitful con artist. Assigned to Europe to retrieve a millionaire’s son, Ripley uses his talents in forgery and impersonation to assume the identity of Dickie (Jude Law).

Still from The Talented Mr. Ripley (Credits: Paramount Pictures)

The character was originally portrayed by Alain Delon in the 1960 classicPlein Soleil. However, it was Damon’s portrayal in the more recent adaptation that brought the role into the spotlight. Recently, Netflix adapted the story into a series withAndrew Scott, but the film remains a memorable favorite among true movie enthusiasts.

The Talented Mr. Ripleyis available to stream on Netflix.

2Rounders(1998)

Roundersis often hailed as one of the best poker movies ever made. It draws viewers into a dramatic story full of revelations and tense moments, offering a deep look into the world of gambling addiction.

In the film, Damon plays Mike McDermott, a poker player who, after losing all his money to the Russian criminal Teddy KGB (John Malkovich), decides to walk away from the gambling scene. However, when his friend Worm (Edward Norton) is released from prison, Mike finds himself drawn back into the world of poker.

Still from Rounders (Credits: Miramax Films)

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The movie is already a standout production, thanks to its rich detail in aspects like poker terminology. However, Damon truly makes a difference with his performance. His charisma brings depth to the role of a brilliant yet unlucky character, keeping the audience hooked as they watch to see just how far he can go.

Roundersis available to stream on Amazon Prime Video.

3The Rainmaker(1997)

Francis Ford Coppolais considered one of cinema’s greatest directors, so landing a role in one of his films is a dream for many actors. Damon achieved this milestone long before he became a Hollywood superstar.

The Rainmakeradapts the literary classic of the same name, following Rudy Baylor, a young unemployed lawyer who not only believes in his dreams but also becomes the last hope for a couple battling the US healthcare system. However, he must contend with far more experienced lawyers on the opposing side of the case.

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Damon received high praise for his lead role, which helped elevate his career and open doors to more promising roles. However, despite the acclaim, the film didn’t achieve box-office success and remains one of his lesser-known works.

The Rainmakeris available to stream on Amazon Prime Video.

4School Ties(1992)

The actor andBen Affleckhave been long-time friends, famously co-writing the classicGood Will Hunting. Their collaboration has also included starring together in several films. However,School Tiesis one of the earliest examples of their partnership, and notably, it doesn’t feature Damon in the lead role.

The movie tells the story of David Greene (Brendan Fraser), a Jewish quarterback recruited by an elite prep school in New England. Damon plays Charlie Dillon, a privileged, anti-Semitic young man who starts to torment the protagonist.

Still from The Rainmaker (Credits: Paramount Pictures)

The film marked Damon’s first significant success and showcased him as one of the rising stars of the time. In this role, he delivers a standout performance as one of his most antagonistic characters to date. It’s one of those films where Damon truly surprises and impresses.

School Tiesis available to stream on Apple TV+.

5Gerry(2002)

Gerryhighlighted the actor’s versatility, showcasing a more experimental side of his talent. The film’s conceptual approach was a departure from the mainstream roles he’s known for. Additionally, Damon went above and beyond by not only acting in the film but also contributing to the script.

It is the most experimental project Damon has ever worked on. The plot doesn’t have much of a storyline, it just comes down to the two protagonists called Gerry walking in the desert, saying practically nothing, to get nowhere.

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This is one of those films that aims to explore the essence of human connection and simplicity without a conventional narrative. The plot encourages viewers to spend time with the characters, immersing themselves in their experiences, sensations, and emotions.

At first, it might seem a bit monotonous, but given that Damon is involved in such a unique project, it becomes one of the most underrated films of his career.

Gerryis available to stream on Amazon Prime Video.

Catherine Delgado

Articles Published :141

A geek enthusiast of fantasy and sci-fi, Catherine is also a screenwriter, completely obsessed with pop culture. Graduated in Audiovisual Production, she creates characters and writes about fictional universes when not writing articles, binge-watching shows, or reading sagas.

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Matt Damon